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[ CAS No. 96036-03-2 ] {[proInfo.proName]}

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Chemical Structure| 96036-03-2
Chemical Structure| 96036-03-2
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Product Details of [ 96036-03-2 ]

CAS No. :96036-03-2 MDL No. :MFCD00864966
Formula : C17H25N3O5S Boiling Point : -
Linear Structure Formula :- InChI Key :DMJNNHOOLUXYBV-PQTSNVLCSA-N
M.W : 383.46 Pubchem ID :441130
Synonyms :
SM 7338
Chemical Name :(4R,5S,6S)-3-(((3S,5S)-5-(Dimethylcarbamoyl)pyrrolidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Safety of [ 96036-03-2 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P272-P280-P284-P302+P352-P304+P340-P333+P313-P342+P311-P362+P364-P501 UN#:2811
Hazard Statements:H317-H334 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 96036-03-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 96036-03-2 ]

[ 96036-03-2 ] Synthesis Path-Downstream   1~3

  • 1
  • 4-nitrobenzyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate [ No CAS ]
  • [ 96034-64-9 ]
  • [ 96036-03-2 ]
YieldReaction ConditionsOperation in experiment
The 4-nitrobenzyl (4i?,5i?,65)-3-[(dirhohenoxyrhohosrhohoryl)oxy]-6-[(li?)-l- hydroxyethyl]-4-methyl-7-oxo-l-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (50 g) and 4- nitrobenzyl (2iS',4JS)-2-[(dimethylamino)carbonyl]-4-mercaptopyrrolidme-l-carboxylate (30 g) obtained from step a) or from step b) were dissolved in a mixture of N5N- dimethylformamide (200 mL) at about 25 0C. The solution was then cooled to -45 0C followed by dropwise addition of diisopropylethylamine (11 g) under stirring while EPO <DP n="14"/>maintaining the temperature between -50 to -45 0C. After stirring the reaction mixture for about 1 hour, it was poured into a mixture of ethyl acetate (500 niL) and water (300 mL). The organic layer was separated and added to a mixture of 5 % palladium on carbon (50 g) in aqueous buffer (500 mL) containing N-methylmorpholine and acetic acid (pH about 7.0). The above biphasic reaction mass was hydrogenated for 3 hours under pressure at 20-25 0C. After completion of the reaction, the mixture was filtered and the aqueous layer was separated. The aqueous layer was concentrated by reverse osmosis and tetrahydrofuran was added to the condensate at a temperature of about 5-10 0C. The resultant mixture was stirred for about 5 hours to obtain the title compound as a trihydrate. Yield: 21.6 g
  • 2
  • [ 93711-81-0 ]
  • [ 96034-64-9 ]
  • [ 96036-03-2 ]
YieldReaction ConditionsOperation in experiment
REFERENCE EXAMPLE Preparation of Meropenem: 4-nitrobenzyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1-R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3 2.0]hept-2-ene-2-carboxylate (Formula VIIIA; 20 g) was dissolved in N-methyl-2-pyrrolidone (100 mL) and cooled to -20 to -150C. 4-Nitrobenzyl (25',4S)-2-[(dimethylamino)carbonyl]-4-mercaptopyrrolidine-l-carboxylate (12 g) was added to the reaction mixture followed by the drop-wise addition of diisopropylethylamine (5.6 g) at -15 to -50C and the reaction mixture was stirred. The reaction mixture was subsequently added to a buffer containing 5% palladium-carbon (30 g) and hydrogenated for 3 to 4 hours at about 250C. (The buffer was prepared using N-methylmorpholine (3.4 g) and appropriate quantity of hydrochloric acid so as to obtain a pH of 6.5 to 7.0 in distilled water (120 mL)). The catalyst was filtered after the completion of hydrogenation and washed with water (100 mL). The filtrate was treated with activated charcoal and acetone (1.6 L) was added to the filtrate at 0 to 50C. The reaction mixture was stirred for 6 hours at 0 to 50C and filtered to obtain the title compound.Yield: 9.8 g Purity: 98% (HPLC)
Reference ExamplePreparation of Meropenem4-nitrobenzyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (Formula VIIIA; 20 g) was dissolved in N-methyl-2-pyrrolidone (100 mL) and cooled to -20 to -15 C. 4-Nitrobenzyl (2S,4S)-2-[(dimethylamino)carbonyl]-4-mercaptopyrrolidine-1-carboxylate (12 g) was added to the reaction mixture followed by the drop-wise addition of diisopropylethylamine (5.6 g) at -15 to -5 C. and the reaction mixture was stirred. The reaction mixture was subsequently added to a buffer containing 5% palladium-carbon (30 g) and hydrogenated for 3 to 4 hours at about 25 C. (The buffer was prepared using N-methylmorpholine (3.4 g) and appropriate quantity of hydrochloric acid so as to obtain a pH of 6.5 to 7.0 in distilled water (120 mL)). The catalyst was filtered after the completion of hydrogenation and washed with water (100 mL). The filtrate was treated with activated charcoal and acetone (1.6 L) was added to the filtrate at 0 to 5 C. The reaction mixture was stirred for 6 hours at 0 to 5 C. and filtered to obtain the title compound.Yield: 9.8 gPurity: 98% (HPLC)
20 g of MAP was dissolved in 80 mL of dimethylacetamide and 12.5 g of the side chain compound was added thereto. After cooling to 0 to 5 C., 6.5mL of diisopropylethylamine was added dropwise. After stirring for 5 hours, 120 mL of ethyl acetate and 200 mL of water were added and the reaction mixture was stirred and then phase-separated. 80 mL of 0.5N HCl was added to the ethyl acetate layer to remove the remaining base, and the resultant mixture was washed with 200 mL of saturated salt water. The remaining water and color were removed by using anhydrous magnesium sulfate and activated carbon. Without the solvent concentration procedure after filtration, the next step was carried out directly in the state of ethyl acetate solution. 60 g of potassium phosphate monobasic (KH2PO4) dissolved in 400 mL of water was added to the ethyl acetate solution and heated to 30 C. or higher. 80 g of zinc powder was added thereto and stirred between 25 and 35 C. for 1 hour. After completion of the reaction, zinc powder was filtered and the filtrate was washed with a mixture solution of tetrahydrofuran/water. The aqueous layer was separated, washed 4 times with 100 mL of methylene chloride and developed in a column filled with adsorption resin SP-207 for adsorption. The resin column was washed with 2 L of water to remove potassium phosphate monobasic used in the reaction and impurities, and developed with 2 L of 60% methanol to elute meropenem completely. The fractions containing meropenem were collected, a buffer solution of N-methylmorpholine/acetic acid (pH 6.5) was added thereto, and concentration was conducted to a volume 10 times greater than the weight of meropenem-PNB. 1100 mL of acetone was added to generate crystal and stirred at room temperature for 1 hour. After filtration and drying, 10.30 g of meropenem trihydrate was obtained.
Example 4 Synthesis of meropenem trihydrate (in situ process) 20g of MAP was dissolved in 80mL of dimethylacetamide and 12.5g of the side chain compound was added thereto. After cooling to 0 to 5C, 6.5mL of diisopropylethylamine was added dropwise. After stirring for 5 hours, 120mL of ethyl acetate and 200mL of water were added and the reaction mixture was stirred and then phase-separated. 80mL of 0.5N HCl was added to the ethyl acetate layer to remove the remaining base, and the resultant mixture was washed with 200mL of saturated salt water. The remaining water and color were removed by using anhydrous magnesium sulfate and activated carbon. Without the solvent concentration procedure after filtration, the next step was carried out directly in the state of ethyl acetate solution. 60g of potassium phosphate monobasic (KH2PO4) dissolved in 400mL of water was added to the ethyl acetate solution and heated to 30C or higher. 80g of zinc powder was added thereto and stirred between 25 and 35C for 1 hour. After completion of the reaction, zinc powder was filtered and the filtrate was washed with a mixture solution of tetrahydrofuran/water. The aqueous layer was separated, washed 4 times with 100mL of methylene chloride and developed in a column filled with adsorption resin SP-207 for adsorption. The resin column was washed with 2L of water to remove potassium phosphate monobasic used in the reaction and impurities, and developed with 2L of 60% methanol to elute meropenem completely. The fractions containing meropenem were collected, a buffer solution of N-methylmorpholine/acetic acid (pH 6.5) was added thereto, and concentration was conducted to a volume 10 times greater than the weight of meropenem-PNB. 1100mL of acetone was added to generate crystal and stirred at room temperature for 1 hour. After filtration and drying, 10.30g of meropenem trihydrate was obtained.

  • 3
  • p-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[(bis(2,4-dichlorophenyl)phosphono)oxy]-1-methylcarbapen-2-em-3-carboxylate [ No CAS ]
  • [ 96034-64-9 ]
  • [ 96036-03-2 ]
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